Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate → methyl 8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxylate

HRID 897354Notes

Reaction equation

HRID 897354 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7](Br)[N:6]=1)=[O:4].[CH3:17][NH:18][S:19]([C:22]1[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=1)(=[O:21])=[O:20]>N1C=CC=CC=1>[OH:15][C:14]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:6][C:7]([N:18]([CH3:17])[S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:20])=[O:21])=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 22343006Methyl 5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylateHCID 22346353HCID 22346353, compound

Product 1

HCID 68898245methyl 8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl-5-bromo-8-hydroxy-1,6-naphthyridine-7-carboxylate (0.969 g, 3.42 mmol), N,1-dimethyl-1H-imidazole-4-sulfonamide (0.60 g, 3.42 mmol) and Cu2O (0.49 g, 3.42 mmol) in pyridine (15 mL) was heated at reflux for 16 hr. The reaction was filtered and the solids washed with CHCl3 (100 mL). The filtrate was stirred for 1 hr with disodium ethylenediamine tetraacetate (1.0 g) in water (20 mL) in the presence of air. The organic extracts were stirred for 1 hr with disodium ethylenediamine tetraacetate (1.0 g in water 20 mL) in the presence of air. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. The residue was suspended in acetonitrile (10 mL) and the resulting solid collected by filtration. The solids were washed with diethyl ether (5 mL) and dried in vacuo to afford the title compound as a solid.

Workup

  1. temperatureat reflux for 16 hr
  2. filtrationThe reaction was filtered
  3. washthe solids washed with CHCl3 (100 mL)
  4. stirringThe organic extracts were stirred for 1 hr with disodium ethylenediamine tetraacetate (1.0 g in water 20 mL) in the presence of air
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. filtrationthe resulting solid collected by filtration
  8. washThe solids were washed with diethyl ether (5 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c992c73a1f8e4e64b73e306359138b98
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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